There’s a woman who lives in my neighborhood who is the most fashionable lady I know. She’s probably in her late 50's, and when I asked my dry cleaner (her dry cleaner, too) if he knew what the woman did for a living, he told me she works at a high school. I’m telling you, I am a full-on fan, nearing stalker status.

What does she do that’s so cool? So much: She understands her body and wears shapes that flatter her—she’s wide in the middle but has long legs so it’s her bottom half that she accentuates. She wears unusual color combinations—like orange and gray, or teal and mauve. She plays with proportion—like pairing a cropped, shrunken jacket over high-waisted super wide leg trousers. She embraces accessories—one day she’ll have on loads of multi-color beads around her neck, another day she’ll don an architectural hat in a vibrant hue.

In short, she is totally unabashed, and I love her for it. Sure, sure, it certainly helps that she obviously has a keen eye for cut, color and design, but the takeaway for all of us (myself included) is to find the fun in fashion and go for it. So what if you get it wrong? Tomorrow is another day and the possibilities are endless.